


Calem Gets Stylish

by SexTheHex



Category: Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters | Pokemon - All Media Types
Genre: Anal, Anal Fingering, Crossdressing, Feminization, Mind Break, Multi, sissification, sissy
Language: English
Status: Completed
Published: 2018-04-15
Updated: 2018-04-15
Packaged: 2019-04-23 08:09:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,432
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14328228
Author URL: https://archiveofourown.org/users/SexTheHex/pseuds/SexTheHex
Summary: Calem is tired of being a nobody. He wants to be stylish! He asks his friend Serena for help in becoming the talk of Lumiose City. However, the price of popularity is pretty steep…





	Calem Gets Stylish

**Author's Note:**

> Originally posted on sexthehex.tumblr.com on 1/5/17.
> 
> The lovely artist sealguy made an amazing piece of art based on this story! You can check it out here: https://sealguy.tumblr.com/post/155700743299

“I-I don’t like this Serena! It’s so embarrassing!” Calem whined.

“Oh calm down now! You’re in a city with thousands of other people, they’ll forget about you in an instant!” Serena insisted “Besides, you want to wear stylish enough clothes to get access to the whole city, right?”

“How is this stylish!? I don’t want this sort of attention!” Calem shouted

Calem had asked Serena for help leveling up his stylishness earlier today. Serena was without a doubt his coolest friend and would know how to get the whole city to know him but crossdressing didn’t seem like it was helping! Calem felt humiliated walking down the street in heals, wearing a pink Bolero dress Serena had picked out for him in Anister. The article of clothing was designed for young girls, not young adults, meaning the hemline of the dress stopped right as his ass ended and his black stocking covered thighs began. Bending over meant exposing his purple panties to any passersby. Cheeks were a feverish red as he endured the degradation.

Why had he agreed to this? All sorts of nasty faces and stares were glaring their way as they trot down the streets of Lumiose. The only thing stopping Calem from running off and getting back in his normal clothes at this point was that he had no idea where he was in the city any more. Leaving Serena’s side meant he’d just be ambling around the city aimlessly, dressed in a ridiculous pink skirt….This city was such a confusing mess that he’d never be able to find where they’d left his blue jacket and pants. With his limited available funds, buying any new clothes wasn’t an option either.

“Having fun yet?” Serena asked.

“No! I want to get out of here and get back into my normal clothes!” Calem pouted.

“Do you really think you’ll become stylish in those drab rags of yours? Please.” Serena explained “You need a new look. You need to shock crowds! Look at all the attention you’re getting! You ought to be thanking me that the whole city’s getting to know your look!”

Calem groaned in annoyance “I-I didn’t want them to know me for THIS! How much longer do I need to stay dressed like this anyway?”

“Just enough to get your name out, you know? I know someone that’ll make sure everyone in the city knows your name~” Serena chimed.

After a tad more walking, the two slipped into a fancy clothing store chock full of designer clothing at dizzying prices. The two ignored the other customers and headed straight for the counter. The cashier instantly recognized Serena, breaking away from the register to allow the two behind the counter into the back area of the store. For how worried Calem was about where Serena was taking him, he was impressed by the power Serena’s style exerted on Lumiose.

The two soon came to the back of the building finding the door to an office. Serena opened it, signaling Calem to enter.

“Get in.” Serena commanded.

Calem stood there for a moment about to ask why he should, but the stern look on Serena’s face said everything. He shuffled into the room, the door slamming behind him. A muffled “Be back soon!” and the pat of footsteps could be heard as the door slammed shut, leaving Calem alone. He swallowed nervously.

“…Ah! So you’re Serena’s newest project then? Gosh, she does have an eye for cuties~” someone called out. Behind the desk of this office was a beauty of a woman, eyes now locked firmly on Calem combing his body up and down.

“Hi… I’m Calem…” he greeted the woman nervously.

“Nice to meet you Calem, I’m Nova. I understand you’re looking to become more stylish, right? You’ve come to the right place! I’m Lumiose’s queen of transformations! I’ll turn you from that ugly boy you use to be into a beautiful, stylish talk of the town!” Nova chimed. “If there’s one thing I’m good at, it’s transforming people. Even myself, really. Yes, a mere half year ago I was a Black Belt! Quite the transformation, wouldn’t you say?”

“O-oh, you mean like a female black belt right?” Calem asked. “Y-yeah, you’ve got such soft features and a shapely body now. I can only imagine how hard it mu-“

“As in a Karate King Black Belt, sweetie.” Nova added “I wanted to be beautiful so I changed every bit of my body, save what’s between my legs.”

“O-oh…” Calem replied, going pale.

“Of course, for you we won’t be doing such drastic things. Initially, at least. If you get into it enough we can doll you up until you look like me, but we’ll start small for now.” Nova explained stepping out from behind her desk and approaching Calem.

“I don’t like this! I want out! I want this to stop now!” Calem yelled, backing up as the woman grew nearer.

Nova backed up at Calem’s request. “Hmm… Well, I can’t force anything on you. However, before you opt out completely, maybe I can show you something to change your mind?” Nova asked, heading back to her desk.

The woman reached into a drawer on her desk and stuffed her hand in. Moments later, Calem’s jaw was agape as Nova sat 100,000 pokedollars on her desk.

“Is that… are you paying me to do this?” Calem asked.

“Mhm. Did you think you wouldn’t be paid handsomely for doing something so strange and demeaning?” Nova asked. “I’m going to teach you about all sorts of lovely pleasures. All you have to do is accept the money, get on your hands and knees, and let me take over for an hour or two.”

Calem stood there for a moment contemplating what he should do. Whatever Nova had planned for him was surely humiliating but… look at all of that money! He could do anything in the city with that kind of cash! Oh what to do, what to do!

After a minute of silence, Calem slowly lowered himself down onto the floor, exposing his panty clad rear to Nova.

“Good girl~” Nova responded.

Suddenly, something about this situation was starting to get to Calem. He was humiliated beyond belief crossdressing and being in such a demeaning position but… he felt a surge of energy in him. It all seemed to awaken with that last little remark. “Good Girl”. There was something to it that just seemed to mess with Calem’s head.

As Nova reached behind her desk to gather something, Calem spoke up.

“C-can you call me that again?” he asked.

“I’m sorry, what?” Nova replied, her head rearing up from behind the desk to answer Calem.

“Can you um… c-can you call me a good girl again?” he asked, his as red as a cherry at the question.

Nova’s smile turned wicked at the question. She grabbed the items she was looking for in her desk, a small bottle of lubricant, and got intimately close to Calem.

“Why do you want me to call you that again?” Nova asked. “Do you like it when I call you that~?”

Calem nodded.

“Do you want Ms. Nova to call you that again? Are you getting all hard at the thought, sweetie?”

Calem nodded faster this time. He had barely noticed up to this point, but he was steadily growing stiff at this exchange.

“Ehehehe~ Are you going to listen to what Ms. Nova says as she opens you up to a new you~?” Nova whispered.

Calem shook his head slowly.

Nova’s head leaned in as close to Calem’s ear as she could before letting out a whisper.

“Good girl~”

“Ah-haaaa…” Calem groaned in excitement. Oh god, what was happening! Why was he so into this? Why was he sitting there motionless!? This was going too far! He wanted to scream “Nevermind! STOP!” as loud as he could but… w-why wasn’t his mouth working!? Why was he sticking around? Worse yet, why was he so hard?”

Nova motioned over to Calem’s rear, giggling as she pulled his purple panties aside and exposed his cute butt to the cool air. Calem let out another groan at the sensation of his panties being removed. He felt so violated… but it felt so wonderful! Everything he knew he should hate he absolutely loved. He wanted… he wanted more! Oh god, he was coming to realize he was a total masochist! He wanted it worse and he couldn’t wait!

Calem’s wishes were soon answered as the cold touch of a lubricated finger tapped his warm virgin anus. Whatever resistance his muscles offered was easily quashed. Nova’s hands moved with such an authoritative, experienced motion that she slid her middle digit into Calem effortlessly. Clearly she’d done this countless times before. And holy fuck did she do it well.

“Haaa-Aaaaah~! Aaaaah… Aaaah…” Calem whimpered. This felt like nothing he’d ever experienced before! He felt helpless as his body completely failed to stop Nova’s fingers from stealing his anal virginity. So wonderfully helpless. So full. He felt like a thing. A thing to be used as others pleased. It was such a divine sensation. The only thing that surpassed it was Nova’s middle finger reaching deep enough into Calem to find his prostate, introducing Calem to the wonders of anal stimulation with that heavenly inaugural press.

Calem’s groans intensified twofold as he felt his p-spot massaged for the first time in his life. His face contorted into a twitching mess of an o-face as he turned into a hopeless groaning mess.

“Good girl~! Goooood Giiiirl~” Nova cooed “It feels so good, doesn’t it sweetie~? Do you like getting your prostate milked~?”

“M-Mmhm” Calem answered through stammering breath.

“Answer me properly sweetie. Use your manners” Nova demanded.

“Y-yes ma’am…” Calem whimpered. He let out a fresh chorus of moans as Nova’s technique transitioned to longer, heavier, firmer strokes.

“Good girl~!” Nova giggled. “You know, this is just a single finger. A hand or a dildo or a fat, meaty cock feels so much better rubbing against there. We’re going to find all sorts of people with big, wonderful dicks to make you go crazy. Serena and I are going to whore you out to every hunk in this city until everyone knows you as Lumiose’s best anal slut!”

Calem went quiet for just a moment. Whoring? Sex with men? He considered himself straight no more than an hour ago. This idea should have been horrifying! The problem was the more he thought about strong, thick cocks pumping his ass and driving him nuts like Nova was now… the more excited he got! It wasn’t disgusting, it was a dream come true! Yes, YES! He was going to be the best ass whore around! He was going to take cocks better than any girl in the city!

Calem’s epiphany caused his constant exhausted moaning to resume, this time with a few attempts at sentences mixed in “Cock… fuck… Fuck… meeee~!” among other weak speech leaked from his mouth in a delirious cock haze. Calem felt wonderful. He was nearly there!

“Oh goodness, you’re such a noisy girl! Do you feel like you’re getting close already?” Nova asked

“Yes ma’a-am” Calem answered

“Do you want to cum from anal, honey? Do you want me to finger fuck your sissy-pussy until you’re drenching the floor in your cum~?” Nova asked, slapping Calem’s ass with a firm smack of the hand.

“Y-yes Ma’am!” Calem yelled with a boundless enthusiasm

Nova intensified the pace of her finger, stroking Calem’s P-spot with the pace of a cock ready to dump its load in a warm wet hole to conclude a furious anal fucking session!

“Then cum honey! Cum like a girl right now!” Nova demanded.

Calem was gasping for breath as the wild sensation of getting his prostate mauled overwhelmed him. This felt a million times better than jerking off! This was really what he wanted after all. There wasn’t any doubt! He couldn’t live without this feeling anymore! He lived for anal! He wanted to be the princess of assfucking!

“Oh-oooooh fuck! Fuck YES! Aaaa-AAAAAAH~!” Calem wined as he felt his body spasm in orgasm, his cock spurting drips of thick white cum from his backdoor cherry popping. Calem could hardly take it. He shoved his face into the carpet and groaned as his first anal orgasm continued, completely amazed by how wonderful it felt.

He was in absolute bliss. He was riding out the orgasmic high of his life and had nothing but more and more of this to look forward to.

—-

Three hours later, Serena returned to the clothing store she’d left Calem, eager to see what Nova’s work had done. After just a moment’s wait, Calem emerged from the back, stunning Serena with his new look.

Calem outright looked like a different person. His figure was now unrecognizable. A pair of strap on DD tits were now weighing him down, filling out the chest of his dress and straining the tiny garment further. A tight corset was squeezing his body, giving him an hourglass appearance. His face was coated in makeup, transforming his rough masculine skin to feminine perfection. His lips were now sporting pink lipstick to match his dress and his hair had been twisted into tiny pigtails. To compliment his new look, Calem was emanating a sultry sense of confidence almost directly opposite of his earlier timid embarrassment.

Nova had done amazing work. A smile grew across Serena’s face as she saw the boy’s new look, quickly approaching him and giving his ass a squeeze.

“Oh gosh, Nova went all out on you, didn’t she honey!” Serena exclaimed, fanning her face at how amazing Calem looked.

“Mhm! I feel like a new woman~” Calem answered back. “Do you like my tits? Nova said if I get stylish enough, maybe a guy will pay for me to get permanent ones!”

“They’re wonderful~” Serena insisted. ”So, ready to work on getting more stylish? I know a guy that runs this fancy sushi restraint that would love to meet you. Getting seen with him is sure to make you the talk of the town!”

“Is he hung?” Calem asked excitedly.

“Like a Mudsdale~ Serena whispered.

Calem grabbed Serena’s hand and happily trotted out of the store, licking his lips in anticipation. Calem really didn’t particularly care anymore about being stylish enough to access every part of the city. Now, his slutty little mind was much more interested in making sure every part of the city had access to every inch of him.


End file.
